Note: Okay, the song is Dido's White Flag and I don't own anything from the show, obviously… so yeah, there you go…

I know you think that I shouldn't still love you or tell you that.
But if I didn't say it well I'd still have felt it,
where's the sense in that
I promise I'm not trying to make your life harder
Or return to where we were but

Rory watched Dean walk away. He was angry, she could tell… of course he was angry… she couldn't tell him that she loved him. Which she did. She felt the words inside – they were on the tip of her tongue… She just couldn't push them out. It had been so easy to tell him before. She'd been so sure of herself. But now…

Jess.

That was the problem. Or maybe he was just the catalyst for their real problem. Maybe he was a good thing for them. It broke up their relationship, forcing them to realize their problems and finally talk about it.

Which brought her to here, watching Dean walk away, his shoulders tense and angry. Of course he was angry. She'd kissed Jess. She was breaking up with him for Jess.

But she didn't know why they were still together. Probably habit. He was just so safe, so comforting, so Dean… it was so easy being with him. Everything was simple with him. Black and white. Never any grey. Life was simple.

Until Jess moved in. And now everything was grey. Everything was complicated. She did like Jess but she knew that she could never love him. He wasn't the type that you just loved… he wasn't the settle down stay together type…

I will go down with this ship and I won't put my hands up and surrender
There will be no white flag above my door,
I'm in love and always will be

Well, she was just stupid. How could she ever think that Jess would be better than Dean? How could she ever think that he would take care of her or care about anything in her life the way that Dean did? He just yelled about how she was always comparing him to Dean, which was legit because she did sometimes but that wasn't the point. He wasn't supposed to think that. He was supposed to believe her that she wanted to be with him and that was why she broke up with Dean… which she had. She'd chosen him over Dean. The problem was that she couldn't convince Jess of that. And the more he talked about it, the more she thought about it… and now she was thinking about Dean constantly. What he was doing now? If he had a new girlfriend? Was he happy? And with that she realized that she was still in love with Dean. And she wasn't going to give that up a second time. She wasn't going to make that mistake again.

I know I left too much mess and destruction to come back again
And I caused but nothing but trouble,
I understand if you can't talk to me again
And if you live by the rules of "it's over" then I'm sure that that makes sense but

Well, it was over. Jess was gone. He'd left on the bus a few hours ago. Rory wasn't really sad. She didn't cry or anything. She'd known, long ago, that it was over. The problem wasn't her and Jess or lack there of. The problem was Dean. She wanted to be with Dean.

But she couldn't.

She'd caused him too much pain, created too much trouble in their relationship – as friends or as boyfriend and girlfriend – to get back into it.

She'd tried to go talk to him but he'd stared at her with burning eyes then turned and walked away, telling her only,

"It's over."

And it made sense. It made all the sense in the world. She'd messed him up. That was a given. Everyone knew that. But there had to be a point where they could find some middle ground. Become friends or something. Try again. Someday.

I will go down with this ship and I won't put my hands up and surrender
There will be no white flag above my door,
I'm in love and always will be

Maybe she was just wishing. Maybe it was fruitless, stupid, and useless. He wasn't going to change his mind. He was strong and determined in his choice. She knew that no matter what she said to him, screamed, begged, cried, it wouldn't change his decision. It would just make it that much harder.

But she wasn't going to give up. Not internally, anyway. She was in love with him. That was something that no one could take from her. He was her first love and would be her last – as Shakespeare as that sounded… it was a fair bit dramatic but she couldn't help it. It was "First Love" syndrome. She had a weak spot for him. He was her weakness.

And when we meet, which I'm sure we will
All that was there, will be there still
I'll let it pass, and hold my tongue
And you will think, that I've moved on....

She saw him again a few years later. She went to Yale, became a journalist, slightly successful, writing for the New York Times – her own column.

He became a lawyer. She was shocked. He'd never said anything about it to her. He'd studied really hard, taken night courses, and gotten into Harvard. The whole town was proud of him. She'd heard so from Loralei during a brief phone call. It had just been thrown in randomly,

"So, I hear that Dean's up in the world these days…" Loralei said mysteriously.

"What?"

"Yeah, turns out the boy had some brains… He's at Harvard!" Loralei said excitedly. She grinned, clutching the phone. What would Rory's answer be?

"That's good for him…" Her insides twisted. Harvard? Dean was at Harvard? She wanted to jump for joy. She was so proud of him. That was amazing… Why though? Why?

Her answer came three days later, standing in a coffee line,

"Rory? Rory Gilmore?"

Turn around. "Dean?" God, he'd changed. Still tall, dark and handsome, he stood out from the crowd in a navy suit and briefcase, the New York Times stuck under his arm. "How are you?"

"Good. And yourself?"

"Good." She could feel the old feelings welling up inside her, the thought mirrored in his eyes. Every memory flowing through her. But she couldn't. They couldn't… "What have you been up to?"

He shrugged, hefting the briefcase. "Work. Lots of work. I'm with Dobson and Dobson now… I guess you heard I went into law?" They both laughed, knowing that in Stars Hollow no secret was safe.

Except mine, she thought darkly. I'm still in love with you, she longed to tell him. But she couldn't. It would just start again, a vicious cycle.

"How about you? How's life?"

She mustered up a smile. "It's good. I'm good."

And that had been it. He'd had to run. A nine o'clock meeting with a client. They promised to keep in touch but it was just too complicated. Phone tag. Brief updates. Too impersonal.

I will go down with this ship and I won't put my hands up and surrender
There will be no white flag above my door,
I'm in love and always will be

But she still loved him. She couldn't help it. He was her first everything, after all… her first kiss, her first boyfriend, her first I love you…


I will go down with this ship and I won't put my hands up and surrender
There will be no white flag above my door,
I'm in love and always will be

Dean ran a hand through his hair, a familiar move to the man after all those years. His co-worker, Ellen, zeroed in on it from across the table, strewn with papers from their latest case. He wasn't thinking about the project. His mind was elsewhere.

"Dean, take a break. You've been working on this project much too hard. Take this weekend off… I'll see you on Monday."

"But we're not even half done," he protested.

She held up a hand. "No, go on. Get out. I'll pull Richmond onto it for this weekend. He owes me…"

He gathered his stuff and left, feeling confused. He drove aimlessly, feeling hollow. Something missing. Something wasn't right. He knew what it was.

Rory.

She was constantly on his mind. He couldn't help it. She was just perfect. He'd had a problem getting back into dating because she was the pedestal that no other woman could ever reach.

He ended up at a coffee shop, the coffee shop, he noticed. The one that he'd seen Rory in the first time he seen her in New York. He noticed a brunette sitting in the window, a familiar brunette. She turned the page of a novel she was completely absorbed in, despite the excitement of a dog knocking over a tray of pastries, people screaming and yelling, coffee and pastries flying everywhere. Parking across the street, he walked quickly towards the coffee shop and Rory Gilmore.

I will go down with this ship and I won't put my hands up and surrender
There will be no white flag above my door,
I'm in love and always will be